4-Chlorophenyl Isocyanate → HCID 131735646, compound

HRID 530625Notes

Reaction equation

HRID 530625 reaction equation
[F:1][C:2]([F:20])([F:19])[C@@H:3]([OH:18])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(#N)C>[ClH:21].[F:20][C:2]([F:1])([F:19])[C@@H:3]([O:18][C:29](=[O:30])[NH:28][C:25]1[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=1)[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH:7]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 117871390HCID 117871390, compound

Product 1

HCID 131735646HCID 131735646, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-1,1,1-Trifluoro-3-(4-methyl-3-phenyl-piperazin-1-yl)-propan-2-ol (180 mg, 0.62 mmol) and 1-chloro-4-isocyanatobenzene (115 mg, 0.75 mmol) were combined in acetonitrile (5 mL). The reaction mixture was stirred overnight and evaporated. The residue was purified by flash chromatography (20/1 dichloromethane/EtOAc then 20/1 dichloromethane/MeOH) to provide the desired product. To the free-base product was added 1M HCl/ether solution to provide HCl salt form, (4-chlorophenyl)-carbamic acid (S)-2,2,2-trifluoro-1-(4-methyl-3-phenyl-piperazin-1-ylmethyl)-ethyl ester hydrochloride (150 mg) as a white solid. (M+H)+=442 m/e.

Workup

  1. customevaporated
  2. customThe residue was purified by flash chromatography (20/1 dichloromethane/EtOAc

Sources & evidence

ORD record
ord-0a0f147859534769ad21d1767782457e
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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